I've been meaning to comment on this.  In iOS 7 this was a failure that 
would just inform us the handshake failed but the replication would work as 
expected.  In iOS 8 the handshake failure was a lot worse as the 
replication wouldn't start until the failure timed out (10 minutes). 
 Here's the error we were receiving.

2014-09-24 17:24:26.426 XXXX[619:261226] CFNetwork SSLHandshake failed 
(-9800)
17:24:26.432‖ WARNING*** : CBLSocketChangeTracker[0x147d9e40 XXXX]: Can't 
connect, giving up: Error Domain=NSOSStatusErrorDomain Code=-9800 "The 
operation couldn’t be completed. (OSStatus error -9800.)"

This was fixed on the server side by hardcoding to always use TLS v1 which 
is supported by iOS 8.  We tried all different combinations of TLS v1.1 and 
v1.2 but the only one that wouldn't cause the problem above was always 
using TLS v1.  This is not an ideal fix but it worked for us.  If anyone 
else finds a more graceful solution please post.

Here's a couple of links that led us to the "solution":
https://github.com/AFNetworking/AFNetworking/issues/2314#issuecomment-56664366
http://stackoverflow.com/questions/25914248/ios-8-has-broken-ssl-connection-in-my-app-cfnetwork-sslhandshake-failed-9806

Jens as usual you were correct in this failure being a lower level problem. 
 :+1:

On Thursday, October 2, 2014 3:08:23 AM UTC-7, rednas wrote:
>
> Did you find a fix for this David? I ran into the same problem. 
>
>

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